It should. I don't see why not. I don't have a TiVo HD yet but see why it would not work. Is you TiVo connected via phone line or broadband? Is it connecting to the service regularly? What happens when you go to click on the Showcases?
Both TiVos connect regularly by broadband. When I go to Showcases and press Info on the HD TiVo, nothing happens, but when I do it on the Series 2 TiVo, it accesses the sweepstakes like it should.
If you look at the fine print on the Star Showcase Sweepstakes it is only offered to S2 users - it doesn't show up on the S3/HD. I have both, it is always only on the S2. Don't know why, though one of the standard prizes is an HD box, so maybe it is a way to get people upgrading? *shrug* But I know I read on the S2 on one of the legalese screens about it being S2 only.
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